Tobacco composition and method of influencing tobacco smoke aroma

ABSTRACT

A tobacco product is treated with a flavoring quantity of a biphenyl or cyclohexyl-cyclohexane compound. The specific effective compounds found suitable for the desired purpose are dodecahydrobiphenyl and 1-methyl-3-cyclohexyl-cyclohexane.

O Umted States Patent 1 3,581,749

[72] Inventors Georg Neurath [50] Field of Search 252/522; 7 Hamburg;260/666; 99/140; I3 H17, 9, I40 I44 Herbert Wichem, Ihlstenbek, both oi,Germany [56] References Cited [2| 1 Appl. No. 842,387 UNITED STATESPATENTS 1 gilcd d y 6 3,246,036 4/1966 Winstrom et al. 260/586 [45]atente une 731 Assignee n. F. Reemtsma & Ph. F. m REFERENCES ParksmGermany Hach s Chemical Dictionary Fourth Edition" (1969) pub. [32]Priority July 2531968 by McGraw-Hill Book Co. NY. p. I94 cited [33]Germany Primary Examiner-Melvin D. Rein [3 l] P 17 92 124.3Attorney-Irving M. Weiner [54] TOBACCO COMPOSITION AND METHOD OFINFLUENCING TOBACCO SMOKE AROMA 3 Claims, No Drawings [52] US. Cl 131/",252/522, 260/666, 99/140, 13 [H44 [51] Int. Cl A24b 15/04 ABSTRACT: Atobacco product is treated with a flavoring quantity of a biphenyl orcyclohexyI-cyclohexane compound. The specific effective compounds foundsuitable for the desired purpose are dodecahydrobiphenyl and l-methyl-3-cyclohexyl-cyclohexane.

TOBACCO COMPOSITION AND METHOD OF INFLUENCING TOBACCO SMOKE AROMA Thepresent invention relates to the treatment of tobacco emphasize thenatural aroma content of the tobacco during smoking.

One object of the invention is therefore the provision of a method oftreating tobacco so as to provide a general emphasizing of the tobaccosmoke aroma.

Methods are already known relating to the aromaticizing of tobacco.Thus, for example the U5. Pat. specifications, Nos. 2,766,145-6C 7describe a method in accordance with which tobacco is treated withlow-molecular weight organic acids which are found themselves, or in theforms of their derivatives, to improve the enjoyment of tobacco smoke.The materials added to the tobacco in accordance with this previousproposal are intended to dominate the flavor of the tobacco smoke.

However, a general reinforcement or emphasizing in accordance with theobject of the present invention is not possible with this previousproposal.

1n accordance with a further proposal tobacco was to be impregnated withmenthol, its derivatives or masked menthol. 1n suitable amounts thementhol passing into the various smoke streams or currents duringsmoking provides a generally fresh flavor in the smoke, but, however,there is no general heightening of the flavor of the impregnatedtobacco. Furthermore, menthol, even when added in small amounts, doesnot harmonize with the various elements responsible for the flavor oftobacco so that many smokers reject it as being an adulteration.

In accordance with a still further prior proposal (see U.S. Pat.specification No. 3,334,637), tobacco goods were to be treated in smallquantities with chemical substances which were to endow the tobacco withcertain elements of flavor. Thus tobacco was, for example, to beimpregnated with lmethyl-2-formyl-pyrrol in order to improve the aroma.in accordance with a further known method (US. Pat. specification No.3,21 1,157) the tobacco had 4-(2-butenylidene)-3, 5, 5trimethyl-Z-cyclohexene-1-one added to it in order to improve theflavor. Finally, in order to provide a cherry flavor, tobacco had2-methyl-5-acetyl-pyrrol added to it.

All these methods are, however, not satisfactory because they either adda flavoring element which is foreign to tobacco, for example cherryflavor, or are so weak in their effect and expensive to provide that thetreatment of tobacco with them, for example with 4-(2-butenylidene)-3,5, S-trimethyl- Z-cyclohexene-l-one bears no proper relation to theimprovement in the tobacco obtained.

The principal object of the invention, that is to say the generalheightening of tobacco, more particularly cigarette tobacco, is achievedin that the flavor of a tobaccolike product is improved by adding to itat least one material of the general formula in which R,, R R and R,,which can be the same or different, denote -H or -CH Such substances arefound to provide with the tobacco with quite unexpected flavorcharacteristics. By tobacco products" we mean tobacco or anothersubstance for burning and inhaling for enjoyment by humans.

The substances, which can be added, by themselves have a fruity smellbut when smoked into tobacco smoke heighten the general flavor of thetobacco and tend to provide a pine flavor which harmonizes well with theother elements in the tobacco flavor.

1n conjunction with conventional tobacco aromaticizing agents such asetheral oils and the like such materials to be added in accordance withthe invention tend to balanceand round off the tobacco flavor whilegenerally emphasizing the aroma so that their use in admixture withconventional flavoring material used in the tobacco industry bringsabout a substantial improvement.

Examples of compounds which can be used in accordance with the inventioninclude dodecahydrobiphenyl and 1- methyl-3-cyclohexyl-cyclohexane.

Dodecahydrobiphenyl has the following characteristics:

Formula C I-1 Bp: 234236 C.

UV: 210 nm.

IR: 2,910, 1,440, 1,350,1,260, 885, 835 cm. MW: 166/ 82,55,83, 67,41

1-methy1-3-cyc1ohexyl-cyclohexane is an example of a methyl derivativeof dodecahydrobiphenyl. The former compound can be produced by thehydrogenation of 2-methyl-4- cyclohexyl-phenol by active nickel inmethane at to C. under pressure (F. Boettcher, Diss. Berlin 1930).Alternatively the compound can be produced vial-methyl-3-phenylcyclohexene-6-one-5by hydrogenation on nickel inmethylcyclohexane at 225 to 245 C. and 50 atm. (Petrow, Anzus, B. 66l933,pages 420 to 422).

The materials to be used in accordance with the invention can be addedto the tobacco in any suitable manner, for example by dipping thetobacco in solutions of the materials or by spraying it at any suitablejuncture during the course of manufacture, for example during theproduction of cigarettes. It is irrelevant as regards the effect on thetobacco smoke flavor whether the whole of the tobacco mixture used for atobacco article, such as a cigarette, is treated or only part ofit.Ifthe alteration in the flavor of the tobacco smoke by one or morematerials in accordance with the invention corresponds with tobaccosnormally added added in order to improve the flavor, such speciallyadded tobaccos can be decreased in quantity or omitted all together.Since such flavoring tobaccos are usually expensive, the invention canthus provide for a decrease in cost.

EXAMPLE 1.

In order to judge the effect on the flavor of tobacco smoke by materialsadded in accordance with the invention, the tobacco mixture forcommercially available cigarettes, which was completely free ofartificial flavoring substances such as etheral oils, was treated with a3 percent ethanolic solution of materials to be added in accordance withthe invention and stored exposed to the air for 48 hours at b 20 C. and67 percent relative humidity and then made into cigarettes. Thecigarette was smoked by a panel of experts and examined as regards thechange in flavor.

The quantity of solution of materials in accordance with the inventionapplied to tobacco mixture was so chosen that the cigarettes of treatedtobacco contained 0.001 percent (or 0.01 percent in the main smokecurrent with respect to the tobacco smoke condensate) of materials to beadded in accordance with the invention. The amount of solution ofmaterial in accordance with the invention was empirically determined.Cigarettes with different proportions of the materials to be addedaccordance with the invention were smoked in accordance with thestandards of the Verband der Zigarettenindustrie" (Beitrage zurTabakforschung 1, page 32 (1961), page 307 (1962) according to DIN draftstandard 10.240) and the main smoke current was analyzed.

Cigarettes treated with dodecahydrobiphenyl were considered, whencompared with untreated control cigarettes, to have a pleasantlyheightened flavor. It was considered that the cigarettes were mild andharmonious in flavor with a slightly peppery background.

EXAMPLE 2:

0 dodecahydrobiphenyl and What we claim is:

l. A method of influencing the flavor of a tobacco product whichinvolves treating the said product with a small amount of an additiveselected from the group consisting of dodecahydrobiphenyl andl-methyl-3-cyclohexyl-cyclohexane, the amount of said additive beingsufficient to effect a change in the tobacco smoke aroma.

2. A tobacco product containing a small amount ofa flavoring additiveselected from the group consisting of l-methyl-3-cycl0hexyl-cyclohexane,the amount of said additive being sufficient to effect a flavor changein the tobacco when smoked.

3. The tobacco product of claim 2 wherein the flavor additiveconstitutes between 0.001 to 1.0 percent by weight of the tobacco.

2. A tobacco product containing a small amount of a flavoring additiveselected from the group consisting of dodecahydrobiphenyl and1-methyl-3-cyclohexyl-cyclohexane, the amount of said additive beingsufficient to effect a flavor change in the tobacco when smoked.
 3. Thetobacco product of claim 2 wherein the flavor additive constitutesbetween 0.001 to 1.0 percent by weight of the tobacco.